Phenyl benzyl ethers, process for producing them and their use as pesticide and fungicide

ABSTRACT

A compound of the general formula I ##STR1## where the indices and the substituents have the following meanings: R 1  is C(CO 2  CH 3 )═CHOCH 3 , C(CO 2  CH 3 )═NOCH 3 , N(OCH 3 )CO 2  CH 3  and C(CONHCH 3 )═NOCH 3  ; 
     R 2  is cyano, halogen, C 1  -C 4  -alkyl and C 1  -C 4  -alkoxy; 
     m is 0 or 1; 
     R 3  is cyano, halogen, C 1  -C 4  -alkyl, C 1  -C 4  -haloalkyl and C 1  -C 4  -alkoxy; 
     n is 0, 1, 2 or 3, it being possible for the substituents R 3  to be different from each other when n is 2 or 3; 
     R 4  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 4  -haloalkyl, C 3  -C 6  -cycloalkyl and phenyl; 
     X and Y are C 1  -C 6  -alkoxy, C 1  -C 6  -alkylthio, C 1  -C 6  -alkylamino, di-C 1  -C 6  -alkylamino or a C 1  -C 4  -alkylene chain which is bonded to the C atom directly or via an oxygen, sulfur and/or nitrogen atom and which can have attached to it one or two of the following substituents: oxo (═O), cyano, C 1  -C 4  -alkyl, C 3  -C 6  -cycloalkyl, C 1  -C 4  -alkoxycarbonyl, aryl and heteroaryl, 
     their preparation and, their use.

This application is a 371 PCT/EP 96/04263 filed on Sep. 30, 1996.

The present invention relates to compounds of the general formula I##STR2## where the indices and the substituents have the followingmeanings: R¹ is C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃and N(OCH₃)--CO₂ CH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0 or 1;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

X and Y are C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁-C₆ -alkylamino or a C₁ -C₄ -alkylene chain which is bonded to the Catom directly or via an oxygen, sulfur and/or nitrogen atom and whichcan have attached to it one or two of the following substituents: oxo(═O), cyano, C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl,aryl and heteroaryl.

Furthermore, the invention relates to processes for the preparation ofthese compounds, to compositions comprising them, and to their use forcontrolling pests or harmful fungi.

Ketones or aldehydes of the phenyl benzyl ethers have been disclosed inthe literature as intermediates (EP-A 513 580; DE-A 43 12 637).

It was an object of the present invention to provide novel activeingredients which have fungicidal and pesticidal properties.

We have found that this object is achieved by the compounds I defined atthe outset. Furthermore, we have found processes for their preparation,compositions comprising them and their use for combating pests orharmful fungi.

The compounds I are prepared by methods similar to those disclosed inthe literature.

For example, compounds I where the radicals X and Y together with the Catom to which they are bonded are an oxirane ring are obtained in amanner known per se [Reactions of Organosulfur Compounds, pp. 101-105,Academic Press, New York 1978; Adv. Org. Chem. 6, 285-388 (1969)] byreacting a carbonyl compound of the formula II with atrimethylsulfoxonium or trimethylsulfonium halide in an inert organicsolvent in the presence of a base. ##STR3##

This reaction is usually carried out at from 0° C. to 150° C.,preferably 20° C. to 120° C.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- andp-xylene, halogenated hydrocarbons such as methylene chloride,chloroform and chlorobenzene, ethers such as diethyl ether, diisopropylether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran,and also dimethyl sulfoxide and dimethylformamide, particularlypreferably dimethyl sulfoxide. mixtures of these can also be used.

Bases which are generally suitable are inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal hydrides and alkaline earth metal hydrides, suchas lithium hydride, sodium hydride, potassium hydride and calciumhydride, organometallic compounds, especially alkali metal alkyls, suchas methyllithium, butyllithium and phenyllithium, alkali metalalcoholates and alkaline earth metal alcoholates such as sodiummethanolate, sodium ethanolate, potassium ethanolate, potassiumtert-butanolate and dimethoxymagnesium. Sodium methoxide, sodiumhydride, sodium hydroxide, potassium hydroxide and potassiumtert-butoxide are particularly preferred.

The bases are generally employed in catalytic amounts, but can also beused in equimolar amounts, in an excess or, if suitable, as solvents.

The carbonyl compounds required for the preparation of the compounds Iare described in the literature cited at the outset. Compounds I wherethe radicals X and Y are bonded to the C atom via an oxygen, sulfur ornitrogen atom and R¹ is C[CONHCH₃ ]═NOCH₃ are obtained, for example, byreacting a carbonyl compound of the formula II in a manner known per se[Synthesis 501-522 (1981), Synthesis 203 (1983); Carboxylic Ortho EsterDerivatives, pp. 154-164, Academic Press, New York 1970] in an inertorganic solvent and optionally an acid and/or an acidic catalyst eithera) with an alcohol, thiol and/or amine of the formula III or b) with acompound of the formula IV. ##STR4##

In formula III, which generally represents compounds of the formulae XHand YH, R^(a) is a C₁ -C₆ -alkyl group. Z in formula III are oxygen,sulfur, amino (NH) or C₁ -C₆ -alkylamino and Z¹ and Z² in formula IV areoxygen, sulfur or amino (NH).

Formula IV represents precursors where X and Y are a C₁ -C₄ -alkylenechain which is bonded to the C atom via oxygen, sulfur and/or nitrogen.Correspondingly, x is 1, 2, 3 or 4 and o is 0, 1, 2 or 3. R is C₁ -C₄-alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano, aryl andheteroaryl or one or more CH₂ groups of the alkylene chain can bereplaced by C═O.

This reaction is usually carried out at from 0° C. to 180° C.,preferably 20° C. to 150° C.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- andp-xylene, halogenated hydrocarbons such as methylene chloride,chloroform and chlorobenzene, ethers such as diethyl ether, diisopropylether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran,nitriles such as acetonitrile and propionitrile, and dimethyl sulfoxideand dimethylformamide, particularly preferably toluene, methylenechloride, chlorobenzene and xylenes.

Mixtures of these can also be used.

Acids and acidic catalysts which may be used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids such as boron trifluoride, tin(IV)chloride, titanium(IV) chloride and zinc(II) chloride, and organic acidssuch as formic acid, acetic acid, propionic acid, oxalic acid, citricacid, trifluoroacetic acid, trifluoromethanesulfonic acid,methanesulfonic acid and toluenesulfonic acid.

The acids, or acidic catalysts, are generally used in catalytic amounts,but can also be used in equimolar amounts, in an excess or, if suitableas the solvent.

Compounds I where R^(a) is not methyl are obtained particularlyadvantageously in a similar manner by first converting the carbonylcompound II with trimethyl formate or methanol to give the correspondingdimethyl acetal or dimethyl ketal (I, X═Y═OCH₃) and subsequentlytransacetalizing this product either with a compound III or with acompound IV. ##STR5##

This reaction of II with trimethyl orthoformate is usually carried outat from 0° C. to 180° C., preferably 20° C. to 150° C.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- andp-xylene, halogenated hydrocarbons such as methylene chloride,chloroform and chlorobenzene, and dimethyl sulfoxide anddimethylformamide, particularly preferably dimethyl sulfoxide anddimethylformamide. Mixtures of these can also be used.

Acids and acidic catalysts which may be used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids such as boron trifluoride, tin(IV)chloride and tin(II) chloride, and organic acids such as formic acid,acetic acid, propionic acid, oxalic acid, citric acid, trifluoroaceticacid, methanesulfonic acid and 4-methylphenylsulfonic acid.

The acids, or the acidic catalysts, are generally employed in catalyticamounts, but they can also be used in equimolar amounts, in an excessor, if suitable, as the solvent.

The educts are generally reacted with each other in equimolar amounts.It may be advantageous for the yield to employ trimethyl orthoformate inan excess or a substoichiometric amount, based on II.

In a further process, the compounds I are also obtained by reacting aphenol of the formula V with a benzyl compound of the formula VI in amanner known per se in an inert organic solvent in the presence of abase. ##STR6##

L in formula VI is a nucleophilically exchangeable group such as halogen(fluorine, chlorine, bromine and iodine, preferably chlorine, bromineand iodine) or an alkyl- or arylsulfonate group (eg. methylsulfonate,trifluoromethylsulfonate, phenylsulfonate and 4-methylphenylsulfonate).

This reaction is usually carried out at from 0° C. to 120° C.,preferably 20° C. to 85° C.

Suitable solvents are ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitritessuch as acetonitrile and propionitrile, ketones such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethylsulfoxide and dimethylformamide, particularly preferablytetrahydrofuran, acetone, acetonitrile, dimethyl sulfoxide anddimethylformamide.

Mixtures of these can also be used.

Bases which are generally used are inorganic compounds such as alkalimetal hydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal oxides and alkaline earth metal oxides such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metalhydrides and alkaline earth metal hydrides such as lithium hydride,sodium hydride, potassium hydride and calcium hydride, alkali metalcarbonates and alkaline earth metal carbonates such as lithiumcarbonate, sodium carbonate, potassium carbonate and calcium carbonateand alkali metal hydrogen carbonates such as sodium hydrogen carbonateand alkali metal alcoholates and alkaline earth metal alcoholates suchas sodium methanolate, sodium ethanolate, potassium ethanolate,potassium tert-butanolate and dimethoxymagnesium, and furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines such as collidine, lutidine and4-dimethylaminopyridine and bicyclic amines.

Sodium hydride, potassium carbonate, sodium methanolate andtriethylamine are particularly preferred.

The bases are generally employed in catalytic amounts, but they can alsobe used in equimolar amounts, in an excess or, if suitable, as thesolvent.

Those starting materials required for the preparation of the compounds Ihave been disclosed in the literature (EP 420 091 A1; EP 38 65 561 A1;DE 36 20 860 A1; DE 35 45 318 A1; WO 93/15046 A1) or can be prepared inaccordance with the literature cited.

Compounds Va where the radicals X and Y are bonded to the C atom via anoxygen, sulfur or nitrogen atom are obtained particularly advantageouslyby first converting a phenol ester of the formula VII in a manner knownper se in an inert organic solvent with a) an alcohol, thiol and/oramine of the formula III or with b) a compound of the formula IV [or, asdescribed above, by first converting it with trimethyl orthoformate ormethanol to give the corresponding dimethyl acetal or dimethyl ketal(VIII, X═Y═OCH₃) and subsequently transacetalizing the product eitherwith a compound III or a compound IV] to give the corresponding phenolester VIII and subsequently cleaving VIII in the presence of a base togive V. ##STR7##

R^(x) in formulae VII and VIII is phenyl or an alkyl group (eg. C₁ -C₄-alkyl).

This ester cleavage is usually carried out at from 0° C. to 120° C.,preferably 0° C. to 80° C.

Suitable solvents are, besides water, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, alcohols such as methanol, ethanol, n-propanol,isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide anddimethylformamide, particularly preferably water, methanol,dimethylformamide, dimethyl sulfoxide and tetrahydrofuran. Mixtures ofthese can also be used.

Bases which are generally used are inorganic compounds such as alkalimetal hydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal oxides and alkaline earth metal oxides such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metalamides such as lithium amide, sodium amide and potassium amide, alkalimetal carbonates and alkaline earth metal carbonates such as sodiumcarbonate, potassium carbonate, calcium carbonate, alkylmagnesiumhalides, such as methylmagnesium chloride and alkali metal alcoholatesand alkaline earth metal alcoholates such as sodium methanolate, sodiumethanolate, potassium ethanolate, potassium tert-butanolate anddimethoxymagnesium, and furthermore organic bases, eg. tertiary aminessuch as trimethylamine, triethylamine, tri-isopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine and 4-dimethylaminopyridine, and bicyclic amines.

Sodium amide, sodium hydroxide, potassium hydroxide and sodiummethanolate are particularly preferred.

The bases are generally employed in catalytic amounts, but they can alsobe used in equimolar amounts, in an excess or, if suitable, as thesolvent.

The reaction mixtures are worked up in the customary manner, eg. bymixing with water, separating the phases and, if desired, purificationof the crude products by chromatography. Some of the intermediates andend products are obtained in the form of colorless or pale brown,viscous oils which can be purified or freed from volatile componentsunder reduced pressure and under moderately elevated temperature. If theintermediates and end products are obtained as solids, they can also bepurified by recrystallization or digestion.

Those starting materials required according to the process describedabove for the preparation of the compounds I which have not already beendisclosed in the literature (Polym. Commun. 337 (1984); EP 353 339 A2)can be prepared in accordance with the literature cited.

Collective terms which generally represent the following substituentsare used in the definitions of the symbols given in the above formulae:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: saturated, straight-chain or branched hydrocarbon radicals having1 to 6 carbon atoms, eg. C₁ -C₆ -alkyl such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

haloalkyl: straight-chain or branched alkyl groups having 1 to 4 carbonatoms (as mentioned above), it being possible for some or all of thehydrogen atoms in these groups to be replaced by halogen atoms asmentioned above, eg. C₁ -C₂ -haloalkyl, such as chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms (as mentioned above) which are bonded to the skeleton via anoxygen atom (--O--);

alkylthio: straight-chain or branched alkyl groups having 1 to 6 carbonatoms (as mentioned above) which are bonded to the skeleton via a sulfuratom (--S--);

alkylamino: a straight-chain or branched alkyl group having 1 to 6carbon atoms (as mentioned above) which is bonded to the skeleton via anamino group (--NH--);

dialkylamino: an amino group which has attached to it two straight-chainor branched alkyl groups which are independent of one another and havein each case 1 to 6 carbon atoms (as mentioned above);

alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 4carbon atoms (as mentioned above) which are bonded to the skeleton viaan oxycarbonyl group (--O--CO--);

cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon atom ringmembers, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

aryl: mono- or polycyclic aromatic hydrocarbons such as phenyl, naphthyland anthracenyl; heteroaryl: mono- or polycyclic aromatic ring systemswhich, besides carbon atoms, can contain nitrogen, oxygen and/or sulfuratoms as ring members, eg.

5-membered heteroaryl having one to four nitrogen atoms or one to threenitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl ringgroups which, besides the carbon atoms, can have one to four nitrogenatoms or one to three nitrogen atoms and one sulfur or oxygen atom asring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl,1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroaryl having one to three nitrogen atoms orone nitrogen atom and one oxygen or sulfur atom: 5-membered heteroarylring groups which, besides carbon atoms, can have one to four nitrogenatoms or one to three nitrogen atoms and one sulfur or oxygen atom asring members and in which two adjacent carbon ring members or onenitrogen and one adjacent carbon ring member can be bridged by abuta-1,3-diene-1,4-diyl group;

5-membered heteroaryl bonded by nitrogen and having one to four nitrogenatoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen andhaving one to three nitrogen atoms: 5-membered heteroaryl ring groupswhich can have, besides carbon atoms, one to four nitrogen atoms, or oneto three nitrogen atoms, respectively, as ring members and in which twoadjacent carbon ring members or one nitrogen and one adjacent carbonring member can be bridged by a buta-1,3-diene-1,4-diyl group, theserings being bonded to the skeleton via one of the nitrogen ring members;

6-membered heteroaryl having one to three, or one to four, nitrogenatoms: 6-membered heteroaryl ring groups which, besides carbon atoms,can have one to three, or one to four, nitrogen atoms as ring members,eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

Compounds I which are especially preferred are those where R¹ is C(CO₂CH₃)═CHOCH₃.

Compounds I which are also preferred are those where R¹ is C(CO₂CH₃)═NOCH₃.

Compounds I which are equally preferred are those where R¹ isC(CONHCH₃)═NOCH₃.

Compounds I which are furthermore preferred are those where R¹ isN(OCH₃)--CO₂ CH₃.

Compounds I which are also particularly preferred are those where m is 0or 1.

Compounds I which are furthermore particularly preferred are those wherem is 1 and R² is cyano, fluorine, chlorine, methyl or methoxy.

Compounds I which are equally particularly preferred are those where nis 1 or 2.

Compounds I which are also particularly preferred are those where R³ ishalogen or C₁ -C₄ -alkyl.

Compounds I which are particularly preferred are those where n is 1 or 2and the radicals R³ are bonded in the 2- or 2,5-position of the phenylring.

Compounds I which are also especially preferred are those where theradical --CXYR⁴ is in the 4- or 5-position of the phenyl ring.

Compounds I which are furthermore particularly preferred are those whereR⁴ is hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl.

Compounds I which are equally particularly preferred are those where Xis C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino and di-C₁ -C₆-alkylamino.

Compounds I which are also particularly preferred are those where Y isC₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino and di-C₁ -C₆-alkylamino.

Compounds I which are furthermore particularly preferred are those whereX and Y together with the C atom to which they are bonded are anunsubstituted or substituted oxirane ring.

Compounds I which are furthermore particularly preferred are those whereX and Y are an unsubstituted or substituted C₂ -C₄ -alkylene chain whichis bonded to the carbon atom via oxygen, sulfur and/or nitrogen atoms.

Equally preferred are compounds I where X and Y together with the C atomto which they are bonded are one of the following heterocycles XY.1 toXY.9: ##STR8## where the bond marked  bond to the phenyl ring and whereo is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, aryl,cyano and heteroaryl or where one or more CH₂ groups of the alkylenechain can be replaced by C═O.

Compounds which are especially preferred are those of the formula I.A##STR9## where the substituents have the following meanings: R¹ is C(CO₂CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

Z¹ and Z² are oxygen, sulfur, amino (NH) or C₁ -C₆ -alkylamino; and

R^(x) and R^(y) are C₁ -C₆ -alkyl.

Compounds which are furthermore especially preferred are those of theformula I.B ##STR10## where the substituents have the followingmeanings: R¹ is C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ andC(CONHCH₃)═NOCH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0.

Compounds which are also especially preferred are those of the formulaI.C ##STR11## where the substituents have the following meanings: R¹ isC(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are furthermore especially preferred are those of theformula I.D ##STR12## where the substituents have the followingmeanings: R¹ is C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ andC(CONHCH₃)═NOCH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are also especially preferred are those of the formulaI.E ##STR13## where the substituents have the following meanings: R¹ isC(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are furthermore especially preferred are those of theformula I.F ##STR14## where the substituents have the followingmeanings: R¹ is C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ andC(CONHCH₃)═NOCH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are also especially preferred are those of the formulaI.G ##STR15## where the substituents have the following meanings: R¹ isC(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are furthermore especially preferred are those of theformula I.H ##STR16## where the substituents have the followingmeanings: R¹ is C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ andC(CONHCH₃)═NOCH₃ ;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano,aryl and heteroaryl or where a CH₂ group of the alkylene chain can bereplaced by C═O.

Compounds which are also especially preferred are those of the formulaI.K ##STR17## where the substituents have the following meanings: R¹ isC(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, aryl andheteroaryl or where a CH₂ group of the alkylene chain can be replaced byC═O.

Compounds which are also especially preferred are those of the formulaI.L ##STR18## where the substituents have the following meanings: R¹ isC(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, N(OCH₃)CO₂ CH₃ and C(CONHCH₃)═NOCH₃;

R² is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

m is 0, 1 or 2, it being possible for the substituents R² to bedifferent from each other when m is 2;

R³ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄-alkoxy;

n is 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3;

R⁴ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl andphenyl;

o is 0, 1, 2 or 3, it being possible for the substituents R to bedifferent from each other when o is 2 or 3; and

R is C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, aryl andheteroaryl or where a CH₂ group of the alkylene chain can be replaced byC═O.

Compounds I which are especially preferred with a view to their use arethose compiled in the tables which follow. Moreover, the groupsmentioned for a substituent in the tables, on their own (independentlyof the combination in which they are mentioned), are considered aparticularly preferred embodiment of the substituent in question.

Table 1

Compounds of the general formula I.1 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring. ##STR19## Table 2

Compounds of the general formula I.2 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring. ##STR20## Table 3

Compounds of the general formula I.3 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring. ##STR21## Table 4

Compounds of the general formula I.4 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring. ##STR22## Table 5

Compounds of the general formula I.1 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 6

Compounds of the general formula I.2 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 7

Compounds of the general formula I.3 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 8

Compounds of the general formula I.4 where m is 0, R³ _(n) is 2-methyland the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 9

Compounds of the general formula I.1 where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 10

Compounds of the general formula I.2 where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 11

Compounds of the general formula I.3 where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 12

Compounds of the general formula I.4 where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 13

Compounds of the general formula I.1 where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 14

Compounds of the general formula I.2, where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 15

Compounds of the general formula I.3, where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 16

Compounds of the general formula I.4, where m is 0, R³ _(n) is 2-fluoroand the combination of the substituents X, Y and R⁴ for a compound is ineach case one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 17

Compounds of the general formula I.1, where m is 0, R³ _(n) is2,5-dimethyl and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 18

Compounds of the general formula I.2, where m is 0, R³ _(n) is2,5-dimethyl and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 19

Compounds of the general formula I.3, where m is 0, R³ _(n) is2,5-dimethyl and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 20

Compounds of the general formula I.4, where m is 0, R³ _(n) is2,5-dimethyl and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 21

Compounds of the general formula I.1, where m is 0, R³ _(n) is 2-methyl,5-chloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 22

Compounds of the general formula I.2, where m is 0, R³ _(n) is 2-methyl,5-chloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 23

Compounds of the general formula I.3, where m is 0, R³ _(n) is 2-methyl,5-chloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 24

Compounds of the general formula I.4, where m is 0, R³ _(n) is 2-methyl,5-chloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 25

Compounds of the general formula I.1, where m is 0, R³ _(n) is2,5-dichloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 26

Compounds of the general formula I.2, where m is 0, R³ _(n) is2,5-dichloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 27

Compounds of the general formula I.3, where m is 0, R³ _(n) is2,5-dichloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 28

Compounds of the general formula I.4, where m is 0, R³ _(n) is2,5-dichloro and the combination of the substituents X, Y and R⁴ for acompound is in each case one line of Table A, the group --CXYR⁴ beingbonded in the 4-position of the phenyl ring.

Table 29

Compounds of the general formula I.1, where m and n are 0, and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 30

Compounds of the general formula I.2, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 31

Compounds of the general formula I.3, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 32

Compounds of the general formula I.4, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the4-position of the phenyl ring.

Table 33

Compounds of the general formula I.1, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 34

Compounds of the general formula I.2, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 35

Compounds of the general formula I.3, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

Table 36

Compounds of the general formula I.4, where m and n are 0 and thecombination of the substituents X, Y and R⁴ for a compound is in eachcase one line of Table A, the group --CXYR⁴ being bonded in the5-position of the phenyl ring.

                  TABLE A                                                         ______________________________________                                                  X          Y           R.sup.4                                      ______________________________________                                        01        OCH.sub.3  OCH.sub.3   H                                              02 OCH.sub.3 OCH.sub.3 CH.sub.3                                               03 OCH.sub.3 OCH.sub.3 CH.sub.2 CH.sub.3                                      04 OCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 H                                    05 OCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.3                             06 OCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.3                  07        CH.sub.2 O         H                                                  08 CH.sub.2 O CH.sub.3                                                        09 CH.sub.2 O CH.sub.2 CH.sub.3                                               10 OCH.sub.2 CH.sub.2 O H                                                     11 OCH.sub.2 CH.sub.2 O CH.sub.3                                              12 OCH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.3                                     13 OCH.sub.2 CH.sub.2 CH.sub.2 O H                                            14 OCH.sub.2 CH.sub.2 CH.sub.2 O CH.sub.3                                     15 OCH.sub.2 CH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.3                            16 CH(CH.sub.3)O H                                                            17 CH(CH.sub.3)O CH.sub.3                                                     18 CH(CH.sub.3)O CH.sub.2 CH.sub.3                                            19 OC(=O)CH.sub.2 O H                                                         20 OC(=O)CH.sub.2 O CH.sub.3                                                  21 OC(=O)CH.sub.2 O CH.sub.2 CH.sub.3                                         22 OC(=O)CH.sub.2 CH.sub.2 O H                                                23 OC(=O)CH.sub.2 CH.sub.2 O CH.sub.3                                         24 OC(=O)CH.sub.2 CH.sub.2 O CH.sub.2 CH.sub.3                                25 OCH.sub.2 CH.sub.2 S H                                                     26 OCH.sub.2 CH.sub.2 S CH.sub.3                                              27 OCH.sub.2 CH.sub.2 S CH.sub.2 CH.sub.3                                     28 SCH.sub.2 CH.sub.2 S H                                                     29 SCH.sub.2 CH.sub.2 S CH.sub.3                                              30 SCH.sub.2 CH.sub.2 S CH.sub.2 CH.sub.3                                     31 SCH.sub.2 CH.sub.2 CH.sub.2 S H                                            32 SCH.sub.2 CH.sub.2 CH.sub.2 S CH.sub.3                                     33 SCH.sub.2 CH.sub.2 CH.sub.2 S CH.sub.2 CH.sub.3                            34 OCH.sub.2 CH.sub.2 CH.sub.2 S H                                            35 OCH.sub.2 CH.sub.2 CH.sub.2 S CH.sub.3                                     36 OCH.sub.2 CH.sub.2 CH.sub.2 S CH.sub.2 CH.sub.3                            37 OCH(CH.sub.3)CH.sub.2 O H                                                  38 OCH(CH.sub.3)CH.sub.2 O CH.sub.3                                           39 OCH(CH.sub.3)CH.sub.2 O CH.sub.2 CH.sub.3                                  40 OCH(CH.sub.3)CH(CH.sub.3)O H                                               41 OCH(CH.sub.3)CH(CH.sub.3)O CH.sub.3                                        42 OCH(CH.sub.3)CH(CH.sub.3)O CH.sub.2 CH.sub.3                               43 OCH(CH.sub.2 CH.sub.3)CH(CH.sub.2 CH.sub.3)O H                             44 OCH(CH.sub.2 CH.sub.3)CH(CH.sub.2 CH.sub.3)O CH.sub.3                      45 OCH(CH.sub.2 CH.sub.3)CH(CH.sub.2 CH.sub.3)O CH.sub.2 CH.sub.3           ______________________________________                                    

The compounds I are suitable for use as fungicides.

The compounds I are distinguished by an outstanding activity against awide spectrum of phytopathogenic fungi, in particular from the classesof the Ascomycetes and Basidiomycetes. Some of them act systemically andcan be employed as foliar- and soil-acting fungicides.

They are particularly important for controlling a large number of fungiin a variety of crop plants such as wheat, rye, barley, oats, rice,maize, grass, cotton, soya, coffee, sugar cane, grape vine, fruitspecies, ornamentals and vegetable species such as cucumbers, beans andcucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphecichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaeraleucotricha in apples, Uncinula necator in grape vines, Puccinia speciesin cereals, Rhizoctonia species in cotton and lawns, Ustilago species incereals and sugar cane, Venturia inaequalis (scab) in apples,Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytiscinerea (gray mold) in strawberries and grape vines, Cercosporaarachidicola in groundnuts, Pseudocercosporella herpotrichoides in wheatand barley, Pyricularia oryzae in rice, Phytophthora infestans inpotatoes and tomatoes, Fusarium and Verticillium species in a variety ofplants, Plasmopara viticola in grape vines, Alternaria species invegetables and fruit.

The compounds I are used by treating the fungi, or the plants, seeds,materials or the soil to be treated against fungal infection, with afungicidally active amount of the active ingredients. Application iseffected before or after infection of the materials, plants or seeds bythe fungi.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the intended purpose in question; in any case,it should guarantee fine and uniform distribution of the compoundsaccording to the invention. The formulations are prepared in a knownmanner, eg. by extending the active ingredient with solvents and/orcarriers, if desired using emulsifiers and dispersants, it also beingpossible to use other organic solvents as auxiliary solvents if water isused as the diluent. Suitable auxiliaries are essentially: solvents,such as aromatics (eg. xylene), chlorinated aromatics (eg.chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg.methanol, butanol), ketones (eg. cyclohexanone), amines (eg.ethanolamine, dimethylformamide) and water; carriers such as groundnatural minerals (eg. kaolins, clays, talc, chalk) and ground syntheticminerals (eg. highly disperse silica, silicates); emulsifiers such asnon-ionic and anionic emulsifiers (eg. polyoxyethylene fatty alcoholethers, alkylsulfonates and arylsulfonates) and dispersants such aslignosulfite waste liquors and methylcellulose.

The fungicidal compositions generally comprise from 0.1 to 95,preferably from 0.5 to 90, % by weight of active ingredient.

Depending on the nature of the desired effect, the rates of applicationare from 0.01 to 2.0 kg of active ingredient per ha.

In the treatment of seed, amounts of from 0.001 to 0.1 g, preferably0.01 to 0.05 g, of active ingredient are generally required per kilogramof seed.

In the use form as fungicides, the compositions according to theinvention can also be present together with other active ingredients,eg. with herbicides, insecticides, growth regulators, fungicides or elsewith fertilizers.

In many cases, a mixture with other fungicides widens the fungicidalspectrum of action.

The following list of fungicides together with which the compoundsaccording to the invention can be applied is intended to illustrate thepossible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron(III)dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc(N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate,2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, di-isopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))-benzimidazole,2-(thiazolyl-(4))-benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide,5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine2-thio-1-oxide, 8-hydroxyquinoline and its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-2,2,2-trichloro-1-(4-morpholinyl)ethylformamide,piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine and its salts,2,6-dimethyl-N-cyclododecylmorpholine and its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and a variety of fungicides such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,hexachlorobenzene, DL-methylN-(2,6-dimethylphenyl)-N-furoyl(2)-alaninate, DL-methylN-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alaninate,N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alaninate,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-[3,5-dichlorophenyl(5-methyl-5-methoxymethyl]-1,3-oxazolidine2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis (4-fluorophenyl) methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are furthermore suitable for efficientlycontrolling pests from the classes of insects, arachnids and nematodes.They can be employed as pesticides in crop protection and in thehygiene, stored-product and veterinary sectors.

The harmful insects include: from the order of the lepidopterans(Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabamaargillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographagamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,Cheimatobia brumata, Choristoneura fumiferana, Choristoneuraoccidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini,Diaphania nitidalis, Diatraea grandiosella, Earias insulana,Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana,Feltia subterranea, Galleria mellonella, Grapholitha funebrana,Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothiszea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeutamalinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygmaexigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar,Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea,Pectinophora gossypiella, Peridroma saucia, Phalera bucephala,Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scabra, Plutella xylostella, Pseudoplusia includens,Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella,Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis,Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana,Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilussinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallussoistitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum,Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchusrufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis,Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus,Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata,Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis,Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrusoryzophilus, Melanotus communis, Meligethes aeneus, Melolonthahippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchussulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotretachrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretanemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus,Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti,Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitiscapitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomyamacellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culexpipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fanniacanicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobiairritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata,Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina,Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscadomestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipulaoleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athaliarosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta,Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata,Solenopsis invicta.

From the order of the heteropterans (Heteroptera), for example,Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercuscingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistusimpictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lyguspratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyantaperditor.

From the order of the homopterans (Homoptera), for example,Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphisfabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicorynebrassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusiapiceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae,Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megouraviciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi,Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphisgraminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteusvitifolii.

From the order of the termites (Isoptera), for example, Calotermesflavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termesnatalensis.

From the order of the orthopterans (Orthoptera), for example, Achetadomestica, Blatta orientalis, Blattella germanica, Forficulaauricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplusbivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplussanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplanetaamericana, Schistocerca americana, Schistocerca peregrina, Stauronotusmaroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) suchas Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilusannulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpusphoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychuscarpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodesrubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychuspilosus, Dermanyssus gallinae, Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus,Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius,Tetranychus urticae.

From the class of the nematodes, for example, root knot nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cystdenematodes, eg. Globodera rostochiensis, Heterodera avenae,Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stemeelworms and foliar nematodes, eg. Belonolaimus longicaudatus,Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchusmulticinctus, Longidorus elongatus, Radopholus similis, Rotylenchusrobustus, Trichodorus primitivus, Tylenchorhynchus claytoni,Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of theirformulations or in the form of the use forms prepared therefrom, eg. inthe form of ready-to-spray solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, materials forspreading, or granules, by means of spraying, atomizing, dusting,spreading or pouring. The use forms depend entirely on the intendedpurposes; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparationscan be varied within wide ranges.

They are in general from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be used very successfully in theultra-low-volume method (ULV), it being possible to apply formulationscomprising more than 95% by weight of active ingredient, or even theactive ingredient without additives.

The application rate of active ingredient for controlling pests is 0.1to 2.0, preferably 0.2 to 1.0, kg/ha under field conditions.

The substances which are suitable for preparing ready-to-spraysolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof wetting agent, adhesive, dispersant or emulsifier. Alternatively, itis also possible to prepare concentrates composed of active substance,wetting agent, adhesive, dispersant or emulsifier and, if desired,solvent or oil, and these concentrates are suitable for dilution withwater.

Suitable surfactants are alkali metal salts, alkaline earth metal saltsand ammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, dibutylnaphthalenesulfonic acid oralkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcoholsulfates and fatty acids and their alkali metal and alkaline earth metalsalts, salts of sulfated fatty alcohol glycol ethers, condensates ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensates of naphthalene or of naphthalenesulfonic acid with phenoland formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers,tributylphenyl polyglycol ethers, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignosulfite waste liquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active ingredients together with a solid carrier.

The formulations in general comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (in accordance with NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention aremixed intimately with a mixture of 92 parts by weight of a pulverulentsilica gel and 8 parts by weight of paraffin oil with which the surfaceof this silica gel has been sprayed. This gives a preparation of theactive ingredient with good adherence properties (comprises 23% byweight of active ingredient).

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture which is composed of 90 parts by weight ofxylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxideto 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calciumdodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil (comprises 9% by weight of activeingredient).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 60 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil(comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel, the mixture is ground in a hammer mill(comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone, and this givesa solution which is suitable for use in the form of microdrops(comprises 90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.Pouring the solution into 100,000 parts by weight of water and finelydistributing it therein gives an aqueous dispersion which comprises0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention aremixed thoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activeingredient.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Examples of solid carriers are mineral earths such as silicagel, silicas, silica gels, silicates, talc, kaolin, attaclay, limestone,lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calciumsulfate and magnesium sulfate, magnesium oxide, ground syntheticmaterials, fertilizers, eg. ammonium sulfate, ammonium phosphate,ammonium nitrate, ureas and products of vegetable origin, such as cerealmeal, tree bark meal, wood meal and nutshell meal, cellulose powders andother solid carriers.

Various types of oils, or herbicides, fungicides, other pesticides andbactericides can be admixed with the active ingredients, if desired onlyimmediately before use (tank mix). These agents can be admixed with theagents according to the invention in a weight ratio of 1:10 to 10:1.

SYNTHESIS EXAMPLES

The protocols given in the synthesis examples below were used forobtaining other compounds I by changing the starting materialsaccordingly. The resulting compounds together with physical data aregiven in the Tables which follow.

Example 1 ##STR23##

3.5 g ofN-methyl-2-[(2'-methyl-4'-acetyl)phenoxymethyl]-phenylglyoxylamideO-methyl oxime (for preparation, cf. DE 43 12 637 A1) together with 0.7g of ethylene glycol, 1.1 g of trimethyl orthoformate and 1 drop ofmethanesulfonic acid are stirred for 24 hours at RT (˜25° C.). Forworking up, the mixture is treated with 0.3 g of 30% strength NaOCH₃solution in methanol, and extracted with water, and the organic phase isconcentrated. The residue is crystallized by stirring with diisopropylether. This gives 2.5 g of the title compound of melting point 94-97° C.

Example 2 ##STR24##

174 g of pyridine followed by 309.3 g of benzoyl chloride are addeddropwise to 300.4 g of 4-acetyl-2-methylphenol. After 1 hour at 40° C.,the mixture is taken up in dilute hydrochloric acid, extracted 1× usingdilute hydrochloric acid, 2× using NaHCO₃ and 2× using water, dried andconcentrated. 514.8 g remain, and this is crystallized by stirring withdiisopropyl ether. IR (cm⁻¹)=1734, 1684, 1268, 1129, 699.

Example 3 ##STR25##

170.4 g of the compound of Example 2 are dissolved in 300 ml ofmethylene chloride, and the solution is treated with 78.2 g of trimethylorthoformate and 0.2 g of methanesulfonic acid. After 120 hours at roomtemperature (RT), a further 3 g of methanesulfonic acid are added andthe mixture is stirred for a further 10 hours at RT. The mixture issubsequently treated with 30% strength NaOCH₃ solution (pH 9),concentrated, taken up in tert-butyl methyl ether, washed 1× usingsaturated NH₄ Cl solution, 3× using saturated NaHCO₃ solution and 2×using water, dried and concentrated. This gives 226 g of product whichis employed in Example 4 without further purification.

Example 4 ##STR26##

226 g of the compound of Example 3, 49 g of ethylene glycol and 6 g ofmethanesulfonic acid are stirred for 24 hours at room temperature (RT)in 1 liter of methylene chloride. The mixture is treated with 30%strength NaOCH₃ solution in methanol (pH=9) and concentrated, and theresidue is taken up in tert-butyl methyl ether. The mixture issubsequently washed with NH₄ Cl solution, 3× using saturated NaHCO₃solution and 2× using water and reconcentrated. This gives 220 g of thetitle compound of an oil. IR (cm⁻¹)=1737, 1267, 1120, 709.

Example 5 ##STR27##

52 g of KOH in 25 g of water are added dropwise to 220 g of the compoundof Example 4. After 1 hour, the mixture is concentrated, the residue istaken up in CH₂ Cl₂ /NH₄ Cl solution, and the mixture is extracted 3×using water, dried and concentrated. 147 g of the title compound remainas an oil. IR (cm⁻¹)=1274, 1122, 1039, 819.

Example 6 ##STR28##

5 g of NaOCH₃ and 100 mg of potassium iodide are added to 4.9 g of thecompound of Example 5 in 30 ml of dimethylformamide. After 1 hour,methyl α-(bromomethylphenyl)-β-methoxy-acrylate (for the preparation,cf. WO 94/05620) in 30 ml of DMF is added dropwise, and stirring iscontinued overnight at room temperature (RT). The mixture issubsequently taken up in CH₂ Cl₂ /water, extracted 3× using water, driedand concentrated. 9.7 g remain, and this is chromatographed over silicagel using toluene/acetone (5:1). This gives 1.5 g of the title compoundas an oil. IR (cm⁻³)=1709, 1632, 1258, 1131, 770.

                                      TABLE                                       __________________________________________________________________________                                                I                                                                               #STR29##                           -                                                                          No.                                                                              R.sup.1   R.sup.2.sub.m                                                                    R.sup.3.sub.n                                                                       # R.sup.4                                                                          X    Y     Physical data*                          __________________________________________________________________________    01 C(NOCH.sub.3)CONHCH.sub.3                                                               -- 2-CH.sub.3                                                                          4 CH.sub.3                                                                         OCH.sub.2 CH.sub.2 O                                                                     94-97                                     02 C(NOCH.sub.3)CONHCH.sub.3 -- 3-CH.sub.3 4 CH.sub.3 OCH.sub.2                                                   CH.sub.2 O 53-56                          03 C(NOCH.sub.3)CONHCH.sub.3 -- 2,5-(CH.sub.3).sub.2 4 CH.sub.3                                                   OCH.sub.2 CH.sub.2 O 141-143                                                   04 C(NOCH.sub.3)CONHCH.sub.3 --                                              2-CH.sub.3 4 CH.sub.3 OCH(CH.sub.3)C                                          H.sub.2 O 96-98                           05 C(NOCH.sub.3)CONHCH.sub.3 -- 3-CH.sub.3 4 CH.sub.3 OCH(CH.sub.3)CH.su                                          b.2 O 84-86                               06 C(NOCH.sub.3)CONHCH.sub.3 -- 2,5-(CH.sub.3).sub.2 4 CH.sub.3                                                   OCH(CH.sub.3)CH.sub.2 O 97-99                                                  07 C(NOCH.sub.3)CONHCH.sub.3 --                                              2-CH.sub.3 4 CH.sub.3 OCH(CH.sub.3)C                                          H(CH.sub.3)O 80-83                        08 C(NOCH.sub.3)CONHCH.sub.3 -- 3-CH.sub.3 4 CH.sub.3 OCH(CH.sub.3)CH(CH                                          .sub.3)O 86-88                            09 C(NOCH.sub.3)CONHCH.sub.3 -- 2,5-(CH.sub.3).sub.2 4 CH.sub.3                                                   OCH(CH.sub.3)CH(CH.sub.3)O 118-120                                             10 C(NOCH.sub.3)CONHCH.sub.3 --                                              2-CH.sub.3 4 CH.sub.3 OCH(CH.sub.2                                            CH.sub.3)CH.sub.2 O 103-105                                                    11 C(NOCH.sub.3)CONHCH.sub.3 --                                              3-CH.sub.3 4 CH.sub.3 OCH(CH.sub.2                                            CH.sub.3)CH.sub.2 O 73-75                 12 C(NOCH.sub.3)CONHCH.sub.3 -- 2,5-(CH.sub.3).sub.2 4 CH.sub.3                                                   OCH(CH.sub.2 CH.sub.3)CH.sub.2 O                                              64-66                                     13 C(NOCH.sub.3)CONHCH.sub.3 -- 2-CH.sub.3 4 CH.sub.3 OCH[(CH.sub.2).sub                                          .2 CH.sub.3 ]CH.sub.2 O 85-87                                                  14 C(NOCH.sub.3)CONHCH.sub.3 --                                              3-CH.sub.3 4 CH.sub.3 OCH[(CH.sub.2)                                          .sub.2 CH.sub.3 ]CH.sub.2 O 79-81                                              15 C(NOCH.sub.3)CONHCH.sub.3 --                                              2,5-(CH.sub.3).sub.2 4 CH.sub.3                                               OCH[(CH.sub.2).sub.2 CH.sub.3                                                 ]CH.sub.2 O 60-62                       __________________________________________________________________________     # Position of group CR.sup.4 XY                                               *m.p. (° C.);                                                     

Examples for the action against harmful fungi

The fungicidal action of the compounds of the general formula I wasdemonstrated by the following experiments:

The active ingredients were prepared as a 10% emulsion in a mixture of70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol®AP6, wetting agent having emulsifying and dispersant action based onethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL,emulsifier based on ethoxylated fatty alcohols) and diluted with waterto give the desired concentration.

Action against Fusarium culmorum

Leaves of wheat seedlings (cultivar "Kanzler") were first treated withthe aqueous preparation of the active ingredients (rate of application:250 ppm). After approximately 24 hours, the plants were treated with aspore suspension of the fungus Fusarium culmorum. The plants which hadthus been treated were subsequently incubated for 6 days at 22-24° C.and a relative atmospheric humidity of >90%. The extent of fungaldevelopment was subsequently determined.

In this test, the disease level of the plants treated with compounds 01,02 and 04 to 15 according to the invention was 15% and less, while thedisease level of the untreated (control) plants was 60%.

Action against Pyricularia oryzae (rice blast)

Rice seedlings (cultivar: "Tai Nong 67") were sprayed to drip point withthe preparation of active ingredient (rate of application: 63 ppm).After 24 hours, the plants were sprayed with an aqueous spore suspensionof the fungus Pyricularia oryzae and kept for 6 days at 22-24° C. at arelative atmospheric humidity of 95-99%. Assessment was carried outvisually.

In this test, the disease level of the plants treated with compounds 01and 03 to 15 according to the invention was 15% and less, while thedisease level of the untreated (control) plants was 75%.

Examples for the action against animal pests

The action of the compounds of the general formula I against animalpests was demonstrated by the following experiments:

The active ingredients were prepared

a. as an 0.1% strength solution in acetone or

b. as a 10% emulsion in a mixture of 70% by weight of cyclohexanone, 20%by weight of Nekanil® LN (Lutensol® AP6, wetting agent havingemulsifying and dispersant action based on ethoxylated alkylphenols) and10% by weight of Emulphor® EL (Emulan® EL, emulsifier based onethoxylated fatty alcohols)

and diluted to give the desired concentration, using acetone in the caseof a. and water in the case of b. After the experiments had beenconcluded, the lowest concentration was determined in each case at whichthe compounds still caused an 80 to 100% inhibition or mortality incomparison with untreated control experiments (limit or minimalconcentration).

We claim:
 1. A compound of the general formula I ##STR30## where theindices and the substituents have the following meanings: R¹ is C(CO₂CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃ and N(OCH₃)--CO₂ CH₃ ;R²is cyano, halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy; m is 0 or 1; R³ iscyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄ -alkoxy; nis 0, 1, 2 or 3, it being possible for the substituents R³ to bedifferent from each other when n is 2 or 3; R⁴ is hydrogen, C₁ -C₄-alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl and phenyl; X and Ytogether with the C atom to which they are bonded form one of thefollowing heterocycles XY.1, XY.3, XY.5 and XY.7 ##STR31## where thebond marked  represents the bond to the phenyl ring and whereo is 0, 1,2 or 3, it being possible for the substituents R to be different fromeach other when o is 2 or 3; and R is C₁ -C₄ -alkyl, oxo(C═O), C₃ -C₆cycloalkyl, C₁ -C₄ -alkoxycarbonyl, cyano, aryl and heteroaryl.
 2. Aprocess for the preparation of compounds I as defined in claim 1 wherethe groups X and Y together with the C atom to which they are bonded arean oxirane ring, which comprises reacting a carbonyl compound of theformula II ##STR32## with a trimethylsulfoxonium or trimethylsulfoniumhalide in a manner known per se in an inert organic solvent in thepresence of a base.
 3. A composition which is suitable for controllingpests or harmful fungi, comprising a solid or liquid carrier and acompound of the formula I as defined in claim
 1. 4. A method ofcontrolling harmful fungi, which comprises treating the fungi, or thematerials, plants, soils or seed to be protected against fungalinfection with an effective amount of a compound of the formula I asdefined in claim
 1. 5. A method of controlling pests, which comprisestreating the pests or the materials, plants, soils or seeds to beprotected against them with an effective amount of a compound of theformula I as defined in claim
 1. 6. A compound of the formula I asdefined in claim 1, where X and Y together with the C atom to which theyare bonded form 1,3-dioxolyl-2 and which may have attached to it one ortwo of the following substituents: oxo (═O), cyano, C₁ -C₄ -alkyl, C₃-C₆ -cycloalkyl, C₁ -C₄ -alkoxycarbonyl, aryl and heteroaryl.